Some Flawed Thoughts About Dating

March 18, 2015


So. I’ve been thinking a lot about relationships.

Lord knows, I’m not an expert on the topic. But after nearly 13 years (!) of awkward courtship in NYC, I’ve encountered my fair share of horrors, consulted many seasoned elders, and learned a thing or 12 along the way. Here are some of my dumber moments and what they (eventually) taught me…

Communication is key.
Everyone knows this, but it can also be tough to put into practice. Games, passive aggression, shady disappearing acts…you name it, I’ve been guilty of it. But in a good situation, you and your mate should strive to speak your truth, with honesty and support — FROM THE VERY BEGINNING. You should feel comfortable saying things like “I want children” or “I am a feminist” and asking questions like “How do you envision the next few years?” and “Are those your scary drugs in the bathroom?” If you don’t communicate your needs, wants and feelings, how will your partner ever know?

Believe what people tell you.
When you’re trying to vet a new mate, remember what everyone from Dr. Ruth to Lena Dunham has reminded us: People tend to tell you the truth about who they are. If a person tells you they’re “just trying to have fun right now,” or they’re not over their ex or they really prefer the company of llamas, listen to them. They’re probably saving you a lot of time and heartbreak.

But remember: Words are cheap.
When I was a child, I had a Samantha doll from the American Girl collection. Back in the 90s, Samantha didn’t wear a frilly pink frock like today’s version. (WTF, American Girl?) She was all business in a starched plaid dress, and carried this needlepoint thing that read “ACTIONS SPEAK LOUDER THAN WORDS.”

While I’d like to think I was a fairly bright child, that sentiment confused me. As a seasoned thirty-something, I totally get it. And nothing could be more true.

It’s not that words aren’t important (see above re communication), but how a person acts is often more telling than their blathering. I once had an ex who promised me the moon, then hit on my friend and forgot my birthday. So look while you listen. Does your person make time for you? Do they want to introduce you to the important people in their life? Last but not least, how do their actions make you feel?

Remember your friends are flawed.
Your friends love you! They want you to wind up with someone wonderful. Someone who will make you happy. Yet, in practice, they may not know what these things look like, never mind how to help you get them.

I once dated this guy who was the openest of books. Early in the relationship, he told me exactly where I stood and how he felt about me, and it was so refreshing. I was over the moon. When I relayed this to my friends, they reacted with such horror that I began to doubt the entire thing. “How intense! Only a complete psycho would say something like that…” Looking back, there was nothing wrong with the guy—he was just emotionally available. My friends were reacting to their own commitment issues, and it totally screwed me up.

Figure out your non-negotiables. Screw everything else.
Do you remember when that book Marry Him came out and everyone got all mad about it? Say what you will about the message (and the controversial essay that spawned it), but there is one awesome piece of advice in there: When envisioning your future mate, you cannot make a list that is 8,356 traits long and then expect to actually find that person. And for that person to like you back.

Ask yourself: What’s really, truly important to you? If you want a partner who’s supportive, funny, wants kids and hearts dogs, then those are your non-negotiables. And maybe it’s cool if their height, hair color and job description are TBD.

While you’re at it, don’t be afraid to venture outside of your type.
I used to have a lot of rules. I wouldn’t date anyone short, since I’m five feet tall and our hypothetical offspring would be Oompa-Loompas. I was afraid to date anyone younger, as I feared they wouldn’t commit. I wanted someone creative, so they would “understand me.” (Rolls eyes at self.) I succeeded in dating lots of old, tall commitment-phobes who suffered for their art.

Then I ventured outside of my “type” and found more meaningful relationships. And I discovered that I actually prefer shorter guys. It’s nice to look a dude in the eye when I’m talking to him, and to not constantly feel like I’m trying to hug a giraffe or scale a Sequoia. Sometimes that thing you didn’t want turns out to be exactly what you needed.

Occasionally, your luck is bad. That does not mean you’re bad.
When I was a senior in college, I developed a crush on a boy in my history class. He read classic literature and wore collared shirts. By all accounts, he seemed sane. I was thrilled when he lingered after class one day to ask if I wanted to grab coffee.

So you can imagine my surprise when he asked, “Are you into dogs?” “Yes! I love dogs!” I replied. Because, you know, I do. “Yeah, but are you, like, into them?” he pressed on. Because I had unwittingly agreed to a date with a dude who was into bestiality. Yes, this actually happened. “What’s wrong with me???” I wailed to my roommate the moment I walked through the door. “Nothing is wrong with you,” she said, “Plenty is wrong with him.”

I’m not suggesting you shirk all blame for whatever goes wrong in your dating life. But sometimes, you can’t take it personally, because it really isn’t about you.

Comparison is the thief of joy.
That’s a thing Theodore Roosevelt said, and a thing I say whenever I look at my Instagram feed. I can be feeling pretty good about my situation…then show me someone donning a big white dress or decorating their lovely new townhouse and I doubt every decision I’ve ever made. Comparison is the surest way to feel lousy—so don’t do it. Not with dates, not with your marital status, not with exes, not with how many Tinder swipes other people get. And if you do accidentally compare, try to remember: Things are never what they seem. Case in point—the “dog guy” from the previous anecdote? He’s now somebody’s husband. Their wedding looked lovely on Facebook, but would you want to be his wife?

Anyway! That seems like a terrible note to end on, does it not? So instead, let us conclude with these lovely words from Oprah, Knower of All Things:

Know that the truth feels right and good and loving.
Love doesn’t hurt, I’ve learned. It feels really good.

At the end of the day, maybe that’s all we need to remember.

(Photo taken earlier this evening, on the Williamsburg Bridge)

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  • I love these flawed thoughts, thank you so much for sharing 🙂

  • Melissa,

    What a great article!

  • Well put! Remembering your friends are flawed is so key … we’re flawed, our friends our flawed, and the people we’re trying to date are flawed. And that’s okay.

  • Thanks for sharing this. My girlfriends and I are all passing it around!

  • What a refreshing and very familiar sounding blog post. Again. Thanks for sharing this stuff! Hugs from your antipode in Belgium (same age – same relationship-fall-apart-timing – and quite the same thoughts here) 🙂

  • Lynn-Holly Fisher Wielenga,

    Lovely! What great things to learn. While your last 13 years might not look like your 12 year old self would have imagined (btw- American girls dolls, best ever.) you’ve learned so much! – about who you are, how to love, and how you want to invest your time and emotions. Incredibly valuable things to learn.
    Thanks for sharing! 🙂

  • thank you for the much needed reminders caroline! nyc dating. sigh.

  • Thanks for writing this!

  • Loved the article! Great reminders

  • I’m just getting out of a five year relationship, so this post comes to me at a perfect time. You’ve hit so many key points I’ve been struggling with. It’s refreshing to see I’m not the only one!

    Thanks for sharing!

    PS: I had Samantha too, and I loved her!!

  • I’m glad you’re writing more! Big fan of your posts and this one specially rings true.
    Beyond dating, a lot of these also work when you meet new people and are trying to become closer to them and get to that place where you can call them “friends.” That can be as tough as dating!

  • Yes yes yes to all of this, especially listening to what people say and then looking at their actions. I also once had a boyfriend who constantly told me how much he loved me and subsequently refused to spend holidays together. I then dated a guy who told me straight-up he wasn’t over his ex and was just looking to have fun, yet I tried to turn it into more. Listening is so key (even if it’s to what they’re not saying!)

  • Love this! I’m tall & date a guy who’s shorter than me & really like it! I’ve seen other tall girls get so wrapped up in the “must be taller than me” mentality they lose sight of the more important things!

    p.s. American Girl has totally gone downhill since they got bought out by Mattel in my opinion 🙂

  • I nearly spat out my drink laughing at the oompa loompa children comment. I’m 5’1 and I NEARLY got together with a guy who’s 5’2. He’s amazing (and a great friend still) but something in me couldn’t do it and I think it was that biological concern for my children. I married a guy who is 6’4 (and perfect for me) but I just identified so much with your comment. I’m new to your blog, I really like it!!

  • Oh my goodness Caroline! I just read your ENTIRE blog from the beginning. You are so refreshingly smart, funny, and honest!I’m looking forward to more posts!

  • Great! I would add another one: find new friends. We usually end up dating guys from around, friends of friends, etc. Not the guy you met at the supermarket. And sometimes you don’t realize the fact that there’s nothing else to explore in your surroundings, everyone is taken or doesn’t fit in your life. Also, big-city guys tend to be less commitment-oriented.

  • Oh Caroline, you beautiful beautiful sunflower :’) Honestly, I’m 19 and I’ve never been in a relationship (prolly cause of religious restrictions) BUT I enjoyed every single thing you wrote in your post. It all made so much sense to me, and I’m a little upset that you haven’t written anything recently :/ WRITE SOMETHING BECAUSE I LOVE YOUR BLOG AND I LOVE ITS MESSAGE. (And I also want to be BFFs with you, the kind who share pictures of their dogs doing silly things with each other) Ok sorry 4 freakin u out. BUT I THINK YOU’RE VERY COOL AND YOU NEED TO WRITE MORE! Okay love you bye! Try to reply to this woman, it’ll make my day :’)

  • Please write more!! Reading from Sydney and love your words and perspective. 🙂

  • Where are you, Caroline? I feel abandoned. I miss your posts. Please come back.

  • Mathilde,

    Hey! I love this post and I love you blog. It is kind of sad that you don’t write here anymore. I also love the articles that you write on Cup of Jo.

  • I love your blog! Its so funny, honest and on point 🙂

  • I really enjoyed reading your blog, I hope you start writing again soon!!

  • come baaaaaaaack.

  • Not related to this post specificially, but thanks for sharing all your feels. Its weird how emotions come in waves, and sometimes just reading how someone is feeling the exact same thing is incredibly comforting.

  • Great great writing! I especially liked the “Believe what people tell you”. So many times it is in hindsight I remember something an ex said that was a clear red flag or deal breaker early on.
    I love your writing, hope to see more~

  • just shared with a friend going through a recent breakup, think you have some really good insights 🙂

  • Caroline, you are such an inspiring human being. I stumbled upon your website around October, while going through a very tough breakup and in a state as fragile as can be. I gotta say, your flawless thoughts which you call flawed just about saved my being an adequate person at that point. So really, thank you so much. I’ve been checking back ever since I first discovered this blog, and it’s a pity you haven’t been posting . . . no pressure, just want to reassure you that if you decide to go back to blogging, I’ll definitely be the first reader in line. ☺️ Sending love all the way from Russia and hoping everything is alright with you!

  • I really wish you would continue updating your blog. I miss it a lot

  • Just a quick one to say I love your writing, I hope you start updating here again now your CoJ days are coming to an end! xx

  • This was SOLID GOLD and exactly what I needed to read today. And so much of it resonated with me, both the funny parts and the sad parts. I am constantly feeling like I’m behind and not at all living the life the way the world expects me to be. But then I remember that I’m living a freaking fantastic life that others would and do envy. Thanks <3

  • Nice article! I tried dating outside my type twice. Neither time worked. It’s pretty much “hit or miss” as most people have a “type” for a reason I suspect.

    Fortunately, I didn’t experience anything like this guy did:
    On the flip side, through my experiences it more so just solidified the reason I have a type and why other types generally haven’t worked for me.